Flavoaffinins, Elusive Cellulose-Binding Natural Products from an Anaerobic Bacterium

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Abstract
Cellulose is the most abundant polymer on Earth. Many anaerobic cellulose-degrading bacteria produce uncharacterized yellow-orange, cellulose-binding pigments known as yellow affinity substances (here referred to as flavoaffinins) that are associated with cellulose degradation. Here, we isolate and structurally characterize the flavoaffinins from Clostridium (Hungateiclostridium) thermocellum, a key workhorse for the industrial conversion of cellulosic feedstocks to ethanol. Flavoaffinins represent an unprecedented structural juxtaposition of an aryl polyene chain with a hydroxy-diene γ-lactone. We also shed light on their biosynthesis using stable-isotope feeding experiments. This effort lays the groundwork for understanding the biological function(s) of the flavoaffinins and expands the limited number of natural products isolated from obligately anaerobic microbes.
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Funding Information
  • Howard Hughes Medical Institute (OPP1158186)
  • Division of Chemistry (CHE-20380529)
  • Bill and Melinda Gates Foundation (OPP1158186)

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